Trifluoroacetic acid → HCID 68181840, compound

HRID 1398676Notes

Reaction equation

HRID 1398676 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[C:13]([N:15]2[C:19]3[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:18]=3[N:17]=[C:16]2[O:25][CH:26]2[CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]2)[CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C>ClCCl>[NH:28]1[CH2:27][CH:26]([O:25][C:16]2[N:15]([C:13]3[CH:12]=[CH:11][N:10]=[C:9]([NH2:8])[N:14]=3)[C:19]3[CH:20]=[C:21]([Br:24])[CH:22]=[CH:23][C:18]=3[N:17]=2)[CH2:29]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 68181663tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate

Product 1

HCID 68181840HCID 68181840, compoundYield 1,130%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL) was added dropwise into a solution of tert-butyl 3-[[1-(2-aminopyrimidin-4-yl)-6-bromo-1H-1,3-benzodiazol-2-yl]oxy]azetidine-1-carboxylate (250 mg, 0.49 mmol, 90%) in dichloromethane (2 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hr. Triethylamine was then added to adjust the pH of the solution to 8. The mixture was concentrated under vacuum to give 2 g (88%) of 4-[2-(azetidin-3-yloxy)-6-bromo-1H-1,3-benzodiazol-1-yl]pyrimidin-2-amine as dark red oil: LC-MS: m/z=+361 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-d702593ebba94d10bd23f1edbcbad059
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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